A fatty acid ester obtained by the formal condensation of egonol with propionic acid. It has been isolated from the fruits of Styrax agrestis.

Identification

IUPAC Names

3-[2-(1,3-benzodioxol-5-yl)-7-methoxy-1-benzofuran-5-yl]propylpropanoate

Molecular Formula
C22H22O6
Mass
382.40650
Monoisotopic Mass
382.14164
Charge
0
InChI
InChI=1S/C22H22O6/c1-3-21(23)25-8-4-5-14-9-16-12-18(28-22(16)20(10-14)24-2)15-6-7-17-19(11-15)27-13-26-17/h6-7,9-12H,3-5,8,13H2,1-2H3
InChIKey
XDGRTOUNCQCWMA-UHFFFAOYSA-N
SMILES
CCC(=O)OCCCc1cc(OC)c2oc(cc2c1)-c1ccc2OCOc2c1
Synonyms

5-(3-propanoyloxypropyl)-7-methoxy-2-(3,4-methylenedioxyphenyl)benzofuran

Species

styrax agrestis

NCBI:txid15352221939219

Europe PubMed Central results


Benzofurans from Styrax agrestis as acetylcholinesterase inhibitors: structure-activity relationships and molecular modeling studies.

Author: Liu J, Dumontet V, Simonin AL, Iorga BI, Guerineau V, Litaudon M, Nguyen VH, Gueritte F.

Abstract: An extract of Styrax agrestis fruits, collected in Vietnam, significantly inhibited acetylcholinesterase (AChE) in vitro. Bioassay-guided fractionation revealed three new egonol-type benzofurans: egonol-9(Z),12(Z) linoleate (1), 7-demethoxyegonol-9(Z),12(Z) linoleate (2), and 7-demethoxyegonol oleate (4). Ten known egonol-type benzofurans were also isolated (3, 5, 6-13). In order to better understand structure-activity relationships in this series, egonol derivatives 14-19 were prepared by chemical modifications and evaluated for their inhibition of AChE, butyrylcholinesterase (BChE), and AChE-induced Aβ aggregation. Compounds 1-4 were the most potent inhibitors of the series, which exhibited inhibitory activity against AChE (IC50 1.4-3.1 μM) and, for 1, Aβ aggregation (77.6%). Molecular docking studies were also performed to investigate interaction of these compounds with the active site of AChE.